期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 22, 页码 11669-11681出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01686
关键词
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资金
- German Research Foundation (DFG) [FR 3848/1-1]
- Latvian Science Council [274/2012]
- INNOVA-BALT project
- Liebig Fellowship (Fonds der Chemischen Industrie)
- Otto-Hahn award program of the Max-Planck society
The indirect (ex-cell) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our ex-cell approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.
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